Earl Sweatshirt first started rapping in the 9th grade in 2008, under the name Sly Tendencies. He posted tracks for his mixtape, Kitchen Cutlery, via MySpace. He and two of his friends (stage names Loofy and Jw Mijo) formed a rap trio called The Backpackerz. They were going to release a mixtape titled World Playground but they eventually disbanded sometime in 2009.

His debut mixtape, Earl, was self-released March 31, 2010 as a free digital download on the Odd Future website.[4] Most of the album was produced by Tyler, The Creator. Earl was named the 24th-best album of 2010 by Complex.[5]

Despite overwhelmingly positive reviews, various sources[6][7][8] indicated that Sweatshirt had stopped making music with Odd Future. Posts from Tyler, The Creator's Twitter and Formspring accounts seemed to indicate that Sweatshirt's mother would not grant permission to release any of Sweatshirt's music; although Earl later expressed in an interview that his mother sent him to Samoa not because of his music or lyrical content, but because of him getting into trouble. Earl attended Coral Reef Academy, a therapeutic retreat school for at-risk boys, located outside of the Samoan capital of Apia.[3][9] At Coral Reef Academy, Earl earned back privileges, and ultimately the opportunity to return home. At the beginning of his enrollment, he had very little freedom and was unable to even use the bathroom unsupervised, but he eventually became a positive role model shown as an example to new students.[10] While there, he read Manning Marable's biography on Malcolm X and Richard Fariña’s counterculture fiction. He also wrote rhymes, including most of his verse on "Oldie," his only contribution to The OF Tape Vol. 2.[11] Earl was brought back from Samoa by Leila Steinberg, the first manager of Tupac Shakur, who today still manages his career.[12]

On December 1, 2011, three formerly unreleased songs by Sweatshirt were released through the OddFutureTalk Odd Future Unreleased mixtape. In December 2011, Sweatshirt was announced as a candidate for XXL's 2012 Freshmen List.[13]

On February 8, 2012, rumors spread around the internet that Sweatshirt had returned to the U.S. when a video of him surfaced on YouTube with a preview of a new song saying if viewers wanted "the full thing" they would have to give him 50,000 followers on Twitter.[14] He also later confirmed on his new Twitter account[15] that he had returned to his home in Los Angeles.[16]

Earl appeared on the song "Oldie" from Odd Future's debut album The OF Tape Vol. 2. This was Earl's return to official Odd Future releases and his first appearance on an Odd Future Records release. On March 20, a video released on the official Odd Future YouTube page featured Earl in a cypher-style music video rapping along to his verse from "Oldie" with the other members of the crew. That same day, Earl performed with the group at the Hammerstein Ballroom in New York City on March 20, 2012.[17] On April 9, 2012, rapper Casey Veggies released a mixtape titled Customized Greatly 3 that included a song featuring Earl Sweatshirt, Tyler the Creator, Domo Genesis, and Hodgy Beats titled "PNCINTLOFWGKTA." During that month Earl Sweatshirt signed on to create his own record label imprint, Tan Cressida, to be distributed through Columbia Records. He turned down several other larger offers due to his priority of remaining close to Odd Future.[3]

On November 2, Earl released his first solo single since his return from Samoa, titled "Chum".[18] On November 12, he announced in a tweet that his debut studio album will be titled Gnossos.[19] On February 21, Earl goes back on Twitter to say that his album will not be called Gnossos.[20] On December 4, Earl announces that the album will instead be called Doris.[21] That same day the music video for track 6 on Doris, "Chum" is posted on YouTube.[22]Doris was reported early on to feature vocals and/or production from Tyler, The Creator, Frank Ocean, Ommas Keith, Thundercat, Domo Genesis, Mac Miller, the Neptunes, Christian Rich, Vince Staples, BadBadNotGood, Pharrell Williams, Samiyam, The Alchemist, Casey Veggies, The Internet and RZA.[23][24][25] On March 6, 2013, while performing with Flying Lotus and Mac Miller, Earl premiered three new songs off Doris: "Burgundy" produced by Pharrell Williams, "Hive" featuring Casey Veggies & Vince Staples and "Guild" featuring Mac Miller. Earl also confirmed the next single to be titled "Whoa" featuring Tyler, The Creator. The song was released to iTunes on March 12, 2013, along with the music video being released, which was directed by Tyler.[26][27][28]

Doris was released on August 20, 2013, under Tan Cressida and Columbia Records. Doris featured guest appearances from Odd Future members Domo Genesis, Frank Ocean, Tyler, the Creator, along with Vince Staples, RZA, Casey Veggies and Mac Miller. Production was primarily handled by Sweatshirt under the pseudonym randomblackdude and production duo Christian Rich. Additional production was provided by Matt Martians, The Neptunes, RZA, Samiyam, BadBadNotGood, Frank Ocean, and Tyler, The Creator. In September 2013, Complex named Sweatshirt the tenth best producer in hip hop.[29] Upon its release, Doris was met with universal critical acclaim from music critics, including perfect scores by The Guardian and Los Angeles Times, which praised Sweatshirt's rhyme schemes and lyrics along with the gritty underground production.[30] The album also fared well commercially debuting at number five on the US Billboard 200 and number one on US Top Rap Albums chart.[31]

On October 10, 2014, Earl confirmed that he had completed the follow-up album to Doris.[32] On November 5, 2014, he released a new song entitled "45" produced by The Alchemist. On February 14, 2015 Earl debuted a new song titled "Quest/Power" via SoundCloud.[33] Earl has been performing unreleased tracks since early 2015, such as "Swamp Vermin", "Vultures", "I Be Outside", "Hell", and "Flowers on the Grave". No specific time table is known for the official releases for these songs.

The full album was released on March 22, 2015, but only the digital version, the physical version was released later on April 14, 2015.[36] A later music video for the song "Off Top" was released on August 7, 2015.[37] Earl stated in an interview with NPR that his record label gave him no notice they would release the album.[38] He says he considers this his first album because he feels he can "back up everything, the good and the bad".

On April 28, 2015, a ten-minute track named "Solace" was released via YouTube, and has gained much attention; gaining more than one-hundred thousand views on YouTube in 24 hours. He stated to NPR that he was making an album called "Solace" inspired by his mother, however many believe it is instead an extended play. The project has not been addressed fully.[39] It is widely debated if Earl left Odd Future or not. It seems he has confirmed he has left through his Twitter on May 28, 2015 by saying "No sympathy for male virgins who're in their feelings about Tyler pointing out and solidifying the obvious" after Tyler, The Creator tweeted what everyone thought was the disbandment of Odd Future, although Tyler denies an Odd Future disbandment. Earl did not appear at Camp Flog Gnaw 2015 on November 14, 2015. Many speculated that Tyler, The Creator did not invite Earl to perform at the Carnival because of a feud or conflict between the two. However, Tyler tweeted the day after the carnival "Thebe and I are fine by the way".

On January 25, 2016, Earl released three new tracks on SoundCloud, "WIND IN MY SAILS", produced by The Alchemist, and "bary" and "SKRT SKRT", produced under his alias 'randomblackdude'. "WIND IN MY SAILS" contains samples from Captain Murphy's song “Children of the Atom" and vocal samples from Gene McDaniels's song "The Parasite (For Buffy)". "bary" contains vocal samples from Kanye West's song "Barry Bonds". "SKRT SKRT" contains vocal samples from 21 Savage's song "Skrrt Skrrt".[40]

On March 4, 2016, Earl was featured on Samiyam's 4th album, Animals Have Feelings. The song, "Mirror", was originally meant for I Don't Like Shit, I Don't Go Outside: An Album By Earl Sweatshirt. According to Earl, The song wasn't included because "The tracklist got fucked up".[41] The music video for "Mirror" was released on June 21, 2016.[42]